An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion
Organic Letters2011Vol. 13(8), pp. 2004–2007
Citations Over TimeTop 10% of 2011 papers
Abstract
Current methods for asymmetric α-arylation require blocking groups to prevent reaction at the α'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.
Related Papers
- → Racemization of Amino Acids in Nature(1982)73 cited
- → [9] In Vivo racemization in mammalian proteins(1984)147 cited
- → Evaluation of Fe and Ru Pincer‐Type Complexes as Catalysts for the Racemization of Secondary Benzylic Alcohols(2016)15 cited
- → Selective racemization of amino acid amides in the presence of amino acids(1986)1 cited
- → Racemization in the Coupling Reaction, Pro-Val+Pro, with the Activated Ester Methods(1973)